Leadership

How to prepare and conduct a skip level meeting

How to prepare and conduct a skip level meeting

TL;DR

  • Seek approval and communicate intentions for a skip-level meeting.
  • Be well-prepared and concise, reflecting positively on your leadership and your boss's decision to hire you.
  • Clearly define expectations and learning objectives
  • Maintain transparency with direct reports about intentions, fostering trust and avoiding surprises.
  • Acknowledge potential delicate situations with direct reports and address concerns proactively.
  • Beware of the risks of unscheduled skip-level meetings to avoid unfavorable perceptions.
  • Approach skip-level meetings with mindfulness, empathy, and consideration for others' interpretations.
  • Strategically navigate skip-level meetings for transformative leadership development and organizational alignment.
  • Thoughtful preparation, transparent communication, and commitment are crucial for successful skip-level engagements.

Skip-level meetings are an essential tool to master. They will help you gain a better perspective of your team and organization. You will be able to better understand bottlenecks, risks, and opportunities for your team and it will help you grow in your leadership career.

Unfortunately, this tool, used improperly can be damaging and hurt both your relationships within the company, as well as your career outlook.

Let's look at how to get the most out of your skip-level meetings and avoid undesirable outcomes.


Part 1: Skip-Level Meeting with Your Boss's Boss

Secure Approval from Your Boss

Before embarking on a skip-level meeting with your boss's boss, it's essential to seek approval. The phrasing matters here. You are not looking for permission, but approval. Foster transparency by clearly expressing your intentions: "I plan to talk to [insert name] to deepen my understanding of my team's role in the whole organization. Is that ok with you? Are there specific topics I should avoid?" This collaborative approach ensures openness and prevents unforeseen concerns.

You do not want to surprise your boss, leaving them feeling like you are undermining their position. Be sure to gain their approval before scheduling the skip-level meeting.

Come Prepared and Be Concise

Your interaction in a skip-level meeting not only reflects on you, but also on your immediate boss. Arm yourself with well-prepared questions and maintain clarity in your communication. While having a set of questions is crucial, frame them as open-ended inquiries to extract insights about their perspective. 

Your thorough preparation contributes positively to the perception of your leadership and your boss's decision to bring you on board.

Define Meeting Expectations

Clearly articulate what you hope to achieve from the skip-level meeting. Whether it's gaining a broader understanding of organizational goals, insights into strategic initiatives, or evaluating communication flows, ensure your goals are well-defined. This clarity not only guides the conversation but also maximizes the value derived from the interaction.

Present your insights

Share the insights you gained from the meeting with your boss. This will help you process the information and give your boss a chance to provide feedback on your learning.


Part 2: Skip-Level Meeting with Reports of Direct Reports

Announce Intentions to Direct Reports:

Maintaining transparency with your direct reports regarding your skip-level meeting is crucial. Communicate your intentions openly: "I plan to talk to [insert name] to deepen my understanding of the whole team. Is there anything I should be aware of? Any topics to avoid?" This proactive communication builds trust and ensures your team feels informed rather than blindsided.

Define Learning Objectives:

Clearly outline what you aim to learn from the skip-level meeting with the reports of your direct reports. Whether it's gaining insights into team dynamics, understanding individual perspectives, or assessing challenges. Having defined learning objectives enhances the effectiveness of the interaction.

Navigate Delicate Situations with Sensitivity:

Acknowledge the potential for delicate situations with your direct reports. If there are challenges or sensitive matters, your involvement may create issues. Address potential concerns openly and proactively, emphasizing your intent to contribute positively and supportively.

Be careful here, not to succumb to the temptation of solving the wrong problems.

Part 3: Cautionary Insights, Scheduling, and Perception

Dangers of Unscheduled Meetings:

Scheduling skip-level meetings without notifying your boss or direct report can lead to unintended consequences. While a well-prepared meeting provides value, an unannounced meeting might be interpreted unfavorably, creating a perception of overreach. Exercise empathy and consider how your actions may be perceived by others.

Mindful and Empathetic Engagement:

A well-prepared skip-level meeting can offer valuable insights into leadership alignment and communication flow. 

Your actions will reflect on your boss or on your direct report respectively. Make sure you reflect on them in a positive manner. Any feedback you might have should be given privately and well-researched.

Conclusion: Strategic Skip-Level Mastery

Skip-level meetings, when approached strategically, can be transformative tools for leadership development and organizational alignment. Navigating this terrain requires thoughtful preparation, transparent communication, and a commitment to fostering positive relationships.